Azido(trimethyl)stannane → HCID 178420385, compound

HRID 392964Notes

Reaction equation

HRID 392964 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:18]3[CH:26]=[CH:27][C:28]([C:30]#[N:31])=[CH:29][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[C:18]3[CH:26]=[CH:27][C:28]([C:30]4[NH:38][N:37]=[N:36][N:31]=4)=[CH:29][C:17]=3[N:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 226607902-[4-(Benzyloxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

Product 1

HCID 178420385HCID 178420385, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of compound 12 (0.041 g, 0.10 mmol) and trimethyltin azide (0.023 g, 0.11 mmol) in toluene (2 mL) was refluxed for 15 h. The reaction mixture was allowed to stand at rt for 48 h. The resulting suspension was filtered and washed with toluene (2×). The solid was treated with hydrogen chloride (4 M in dioxane, several mL) for 4 h at rt. The reaction mixture was concentrated on a rotary evaporator. The residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid) to afford 13 as a white solid (0.009 g, 20%). 1H NMR (CDCl3) δ 8.22 (br s, 1H), 8.05 (br m, 1H), 7.82 (br m, 3H), 7.52-7.38 (m, 5H), 7.30 (br m, 2H), 5.23 (s, 2H), 4.53 (br m, 1H), 2.27 (br m, 4H), 2.06 (br m, 2H), 1.84 (br m, 1H), 1.40 (br m, 3H); ESI-MS m/e 451.3 (M+1); HPLC purity (ELSD)>95%.

Workup

  1. temperaturewas refluxed for 15 h
  2. filtrationThe resulting suspension was filtered
  3. washwashed with toluene (2×)
  4. additionThe solid was treated with hydrogen chloride (4 M in dioxane, several mL) for 4 h at rt
  5. concentrationThe reaction mixture was concentrated on a rotary evaporator
  6. customThe residue was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-57347641a7f24669b1426a447d0b47fa
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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